Sodium Hydroxide → 3-Tert-butyl-2-methoxybenzoic acid

HRID 66390

Reaction equation

HRID 66390 reaction equation
[C:1]([C:5]1[C:6]([O:12][CH3:13])=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:15].[K+].[OH-:20].[Na+]>>[C:1]([C:5]1[C:6]([O:12][CH3:13])=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:11]([OH:15])=[O:20])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium Permanganate2×HCID 521940Benzene, 1-(1,1-dimethylethyl)-2-methoxy-3-methyl-

Product 1

HCID 156915293-Tert-butyl-2-methoxybenzoic acid

Procedure

A mixture of 0.01 mole of 3-t-butyl-2-methoxytoluene, 0.01 mole of potassium permanganate, and 100 ml. of 1 N sodium hydroxide solution is heated to reflux and another 0.01 mole of potassium permanganate is added each hour until a total of 0.05 mole has been added (4 hours). After another 2 hours of reflux the unreacted starting material is steam distilled. Ethanol is added to the residue to decompose excess permanganate and mixture is filtered hot. Acidification with sulfuric acid of the filtrate causes precipitation of the product which is collected, washed with water and dried to give 3-t-butyl-2-methoxybenzoic acid.

Workup

  1. temperatureto reflux
  2. additionhas been added (4 hours)
  3. temperatureAfter another 2 hours of reflux the
  4. distillationdistilled
  5. additionEthanol is added to the residue
  6. filtrationis filtered hot
  7. customprecipitation of the product which
  8. customis collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-8df6ebcac1a34b6a99dcb45e49349429
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Linked notes

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